Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 7, 2019
Previous Article Next Article

Iron-catalyzed protodehalogenation of alkyl and aryl halides using hydrosilanes

Author affiliations

Abstract

A simple and efficient iron-catalyzed protodehalogenation of alkyl and aryl halides using phenylhydrosilane is disclosed. The reaction utilizes FeCl3 without the requirement of ligands. Unactivated alkyl and aryl halides were successfully reduced in good yields; sterically hindered tertiary halides were also reduced including the less reactive chlorides. The scalability of this methodology was demonstrated by a gram-scale synthesis with a catalyst loading as low as 0.5 mol%. Notably, disproportionation of phenylsilane leads to diphenylsilane that further reduces the halides. Preliminary mechanistic studies revealed a non-radical pathway and the source of hydrogen is PhSiH3via deuterium labeling studies. Our methodology represents simplicity and provides a good alternative to typical tin, aluminum and boron hydride reagents.

Graphical abstract: Iron-catalyzed protodehalogenation of alkyl and aryl halides using hydrosilanes

Back to tab navigation

Supplementary files

Article information


Submitted
23 Sep 2018
Accepted
01 Nov 2018
First published
02 Nov 2018

Org. Biomol. Chem., 2019,17, 1749-1753
Article type
Communication

Iron-catalyzed protodehalogenation of alkyl and aryl halides using hydrosilanes

R. Pilli, V. Balakrishnan, R. Chandrasekaran and R. Rasappan, Org. Biomol. Chem., 2019, 17, 1749
DOI: 10.1039/C8OB02365D

Social activity

Search articles by author

Spotlight

Advertisements